Water → HCID 21930356, compound

HRID 1178532Notes

Reaction equation

HRID 1178532 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:14][C:15]1[C:16]([O:23][CH3:24])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH:18]([C:17]1[C:16]([O:23][CH3:24])=[C:15]([CH:22]=[CH:21][CH:20]=1)[O:14][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Product 1

HCID 21930356HCID 21930356, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-trifluoromethyl-benzonitrile (0.56 mL, 0.76 g, 4 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.61 g, 4 mmol) and cesium carbonate (1.3 g, 4 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 18 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with water (2×), 10% sodium carbonate solution (2×), water (1×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-(3-formyl-2-methoxy-phenoxy)-4-trifluoromethyl-benzonitrile (1.17 g, 91%) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with water (2×), 10% sodium carbonate solution (2×), water (1×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c9e0ba780f347218373317359801110
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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